Acetic Acid → 5-[4-(2-Hydroxyethyl)piperazin-1-ylmethyl]indole

HRID 20978

반응식

HRID 20978 반응식
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)=O.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.[OH:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.CN(C1C=CN=CC=1)C.O>[OH:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][N:33]([CH2:1][C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][CH:7]=[CH:6]3)[CH2:32][CH2:31]1

참가 물질

10

반응물 6

HCID 176Acetic AcidHCID 76771-(2-Hydroxyethyl)piperazineHCID 10340Sodium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 589040Indole-5-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 684922255-[4-(2-Hydroxyethyl)piperazin-1-ylmethyl]indole수율 132.2%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6342Acetonitrile용매2회

실험 절차

5-Formylindole (2.00 g, 13.8 mmol) was dissolved in acetonitrile (40 mL), and the solution was added with di-tert-butyldicarbonate (3.31 g, 15.2 mmol) and DMAP (16.8 mg, 0.138 mmol), followed by stirring at room temperature for 2.7 hours. The solution was added with a solution of N-(2-hydroxyethyl)piperazine (6.46 g, 49.6 mmol) in acetonitrile (15 mL), and acetic acid (14.2 mL, 248 mmol), then sodium triacetoxyborohydride (13.1 g, 62.0 mmol) was added thereto little by little, followed by stirring at room temperature for 2.5 hours. The reaction mixture was added with water and sodium carbonate to adjust the pH to 9, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (chloroform/methanol=9/1, 4/1) to obtain 5-[4-(2-hydroxyethyl)piperazin-1-ylmethyl]indole (4.73 g, yield 95%).

후처리

  1. stirringby stirring at room temperature for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography (chloroform/methanol=9/1, 4/1)

출처 및 근거

ORD 기록
ord-a23f19c4c3e742429592b0df512d02f8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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